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Chemical Structure| 861841-90-9 Chemical Structure| 861841-90-9

Structure of 861841-90-9

Chemical Structure| 861841-90-9

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Product Details of [ 861841-90-9 ]

CAS No. :861841-90-9
Formula : C15H15NO3
M.W : 257.28
SMILES Code : CC(C1=CC(OCC2=CC=CC=C2)=CC(N)=C1O)=O
MDL No. :MFCD22570434
InChI Key :VHNDAASEYRABBJ-UHFFFAOYSA-N
Pubchem ID :21072822

Safety of [ 861841-90-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 861841-90-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 861841-90-9 ]
  • Downstream synthetic route of [ 861841-90-9 ]

[ 861841-90-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 861841-90-9 ]
  • [ 79-04-9 ]
  • [ 869478-09-1 ]
YieldReaction ConditionsOperation in experiment
50% at 0 - 20℃; Heating / reflux 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while being cooled with the ice bath.
Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature.
The hot reaction mixture is filtered, then evaporated down to approx.
400 mL and combined with ice water.
The precipitate obtained is suction filtered, dried and purified by chromatography on a short silica gel column (dichloromethane:methanol=99:1).
The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]+=298.
50% at 0 - 20℃; Heating / reflux c) 8-acetyl-6-benzyloxy-4H-benzo[1,4]oxazin-3-one: 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while cooling with the ice bath. Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature. The hot reaction mixture is filtered, then evaporated down to about 400 mL and combined with ice water. The precipitate formed is suction filtered, dried and purified chromatography on a short silica gel column (dichloromethane:methanol=99:1). The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]+=298.
17.53 g With potassium carbonate In acetonitrile for 20 h; Reflux 1000 ml three-neck bottle in, under the condition of ice, to compounds 1 - 7 (159 mmol), potassium carbonate (65.8 g, 477 mmol) of acetonitrile (700 ml) solution adds by drops the chlorine acetyl chloride (27 g, 238 mmol), room temperature reaction 4 h, continue to heating to reflux the reaction 16 h. The condiments filtering, the filtrate is concentrated to 200 ml, is added to the 1 L ice water, ice bath conditions for the continuation of stirring 1 h, filtered, washed with water, drying. The resulting solid silica gel column purification (dichloromethane: methanol=99:1), after concentration isopropyl alcohol/methyl cyclohexane recrystallized, filtering to obtain light brown color solid product 17.53 g.
References: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1410 - 1414.
[2] Patent: US2005/267106, 2005, A1, . Location in patent: Page/Page column 7.
[3] Patent: WO2005/111005, 2005, A1, . Location in patent: Page/Page column 16.
[4] Patent: US2007/249595, 2007, A1, . Location in patent: Page/Page column 11.
[5] Patent: US2007/88160, 2007, A1, . Location in patent: Page/Page column 11.
[6] Patent: US2005/255050, 2005, A1, .
[7] Patent: US2010/22770, 2010, A1, . Location in patent: Page/Page column 6.
[8] Patent: CN107188865, 2017, A, . Location in patent: Paragraph 0051; 0062; 0063.
 

Historical Records

Technical Information

• Acidity of Phenols • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Grignard Reaction • Halogenation of Phenols • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Nomenclature of Ethers • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Reimer-Tiemann Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 861841-90-9 ]

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